methyl (2R,3S)-3-O-t-butyldimethylsilyl-3-hydroxy-2,4-dimethylpentanoate | 308795-28-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R,3S)-3-O-t-butyldimethylsilyl-3-hydroxy-2,4-dimethylpentanoate
• 英文别名: methyl (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethylpentanoate
• CAS: 308795-28-0
• 化学式: C₁₄H₃₀O₃Si
• 分子量: 274.476
• InChiKey: BPASNSPPHRGKNT-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2R,3S)-3-O-t-butyldimethylsilyl-3-hydroxy-2,4-dimethylpentanoate 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以80%的产率得到[2R,3S]-(+)-methyl-3-hydroxy-2,4-dimethyl-pentanoate
  参考文献：
  名称：

  Stereoselective synthesis of syn-α-methyl-β-hydroxy esters

  摘要：

  Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2-sqn/1,3-syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O-formylated syn-alpha-methyl-beta-hydroxy esters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone behaves therefore as a chiral propionate enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00274-3
• 作为产物：
  描述：

  (2S,4R,5S)-1,2-O-cyclohexylidene-5-O-t-butyldimethylsilyl-1,2,5-trihydroxy-4,6-dimethylheptan-3-one 在 高碘酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 生成 methyl (2R,3S)-3-O-t-butyldimethylsilyl-3-hydroxy-2,4-dimethylpentanoate
  参考文献：
  名称：

  Stereoselective synthesis of syn-α-methyl-β-hydroxy esters

  摘要：

  Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2-sqn/1,3-syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O-formylated syn-alpha-methyl-beta-hydroxy esters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone behaves therefore as a chiral propionate enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00274-3